Deoxyvulgarin | 3650-22-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Deoxyvulgarin
• 英文别名: (3S,3aS,5aR,9aS,9bS)-3,5a,9-trimethyl-3a,4,5,7,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-2,6-dione
• CAS: 3650-22-4
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: QSLAKERDFMJVOF-KKQCIPQASA-N

物化性质

• 熔点：
  134-136 °C
• 沸点：
  402.9±40.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Deoxyvulgarin 生成 11,13-dihydrosantamarin
  参考文献：
  名称：

  Biomimetic synthesis of 5α-hydroxy-guaianolides

  摘要：

  DOI：

  10.1016/s0040-4039(00)84640-7
• 作为产物：
  描述：

  vulgarin 在 溶剂黄146 、 锌 作用下， 以85%的产率得到Deoxyvulgarin
  参考文献：
  名称：

  Partial synthesis of germacranolides with pyran and furan-type rings

  摘要：

  Pathways to synthesize germacranolides with ether bridges between C1 and C5 or C3 and C-10 were described. A joint precursor was prepared using a readily available and inexpensive compound as starting material. The key step in the preparation of dihydropyranone-germacranolides proved to be a one-pot procedure involving several transformations, induced by the iodotrimethylsilane/acetonitrile system.

  DOI：

  10.1016/s0040-4039(00)61275-3

文献信息

• TOTAL SYNTHESES OF MOKKO LACTONE, DEHYDROCOSTUS LACTONE, AND EREMANTHIN
  作者：Masayoshi Ando、Akio ONO、Kahei Takase

  DOI：10.1246/cl.1984.493

  日期：1984.4.5

  A series of guaianolides such as mokko lactone, dehydrocostus lactone, and eremanthin which posses a common structural unit in A ring have been synthesized from 1-oxoeudesm-2-eno-13,6α-lactone in 7 steps. The key step involves solvolytic rearrangement of 1β-mesyloxyeudesm-4(14)-eno-13,6α-lactone.

  以1-oxoeudesm-2-eno-13,6α-内酯为原料，经过7步合成了一系列在A环上具有共同结构单元的愈创木酚内酯，如木香内酯、脱氢木香内酯和eremanthin。关键步骤涉及 1β-mesyloxyeudesm-4(14)-eno-13,6α-内酯的溶剂分解重排。
• Biogenetic-type synthesis of vulgarin and peroxyvulgarin
  作者：Mansour S. Al-Said、Sherief I. Khalifa、Farouk S. El-Feraly、Charles D. Hufford

  DOI：10.1016/0031-9422(89)85018-6

  日期：——

  Abstract The eudesmanolides vulgarin and peroxyvulgarin were obtained via a biogenetic-type route that involved photo-oxygenation of 1-oxo-5αH,6,11βH-eudesm-3-en-6, 12-olide. The α-face singlet oxygen ( 1 O 2 ) attack resulted in the production of peroxyvulgarin as the major product. Stannous chloride reduction of that compound readily yielded vulgarin. These two compounds, vulgarin and peroxyvulgarin

  摘要 eudesmanoides vulgarin 和peroxyvulgarin 是通过生物遗传型途径获得的，该途径涉及1-oxo-5αH,6,11βH-eudesm-3-en-6, 12-olide 的光氧化。α 面单线态氧 ( 1 O 2 ) 攻击导致产生了作为主要产物的过氧化物。该化合物的氯化亚锡还原很容易产生俗称。这两种化合物，vulgarin 和peroxyvulgarin，是从Artemisia abyssinica 中分离出来的。
• Syntheses and structure-activity relationship study of santamarine, douglanine, dihydrosantamarine and four series of 1-/3-oxygenated eudesman-12,6α-olides
  作者：Rui Wang、Daisuke Toyama、Kei Arao、Miwako Shinozaki、Mariko Ando、Yuhua Bai、Masayoshi Ando

  DOI：10.1016/j.tet.2022.132912

  日期：2022.8

  Herein, we report the syntheses and structure-activity relationships of Santamarine, Douglanine, dihydrosantamarine, 1-oxygenated and 3-oxygenated eudesman-12,6α-lactones. The anti-inflammatory and anti-cancer activities were measured by the inhibition on induction of intercellular adhesion molecule (ICAM-1), killing function of cytotoxic T lymphocytes (CTLs), and cytotoxic activities to cell lines

  在此，我们报告了 Santamarine、Douglanine、dihydrosantamarine、1-氧化和 3-氧化 eudesman-12,6 α -内酯的合成和构效关系。通过抑制细胞间粘附分子（ICAM-1）的诱导，细胞毒性T淋巴细胞（CTL）的杀伤功能和对细胞系（VA-13，HepG-2）的细胞毒活性来测量抗炎和抗癌活性, 和 WI-38), 分别。具有 1-oxo-2-en 部分的α -Methylene- γ -lactones 13对 ICAM-1 (IC 50 12.8 μM)、CTLs (IC 50 11.0 μM) 和 VA-13 细胞系的杀伤功能具有显着抑制作用(IC 50 2.84 μM), 21α-溴酮部分对 VA-13 有显着抑制作用(IC 50 1.85 μM)。13个（（细胞活力）/（ICAM-1 的抑制活性）= 6.0 倍，WI-38/VA-13 = 1
• Studies on the syntheses of sesquiterpene lactones. 8. Syntheses of saussurea lactone, 8-deoxymelitensin, and 11,12-dehydro-8-deoxymelitensin via a novel fragmentation reaction
  作者：Masayoshi Ando、Kiyoshi Tajima、Kahei Takase

  DOI：10.1021/jo00156a014

  日期：1983.4
• Guaianolides as Immunomodulators. Synthesis and Biological Activities of Dehydrocostus Lactone, Mokko Lactone, Eremanthin, and Their Derivatives
  作者：Saori Yuuya、Hisahiro Hagiwara、Toshio Suzuki、Masayoshi Ando、Atsushi Yamada、Kouji Suda、Takao Kataoka、Kazuo Nagai

  DOI：10.1021/np980092u

  日期：1999.1.1

  The naturally occurring guaianolides, namely mokko lactone (1), dehydrocostus lactone (2), eremanthin (3), and related guaianolides, 16, 17, 21, 22, 28-31, 33, 36, 37, and 39, have been synthesized starting from I-a-santonin in an effort to examine their structure-activity relationship as inhibitors of the killing function of cytotoxic T lymphocytes (CTL) and the induction of intercellular adhesion molecule-1 (ICAM-1). It was observed during the present study that the guaianolides possessing an alpha-methylene gamma-lactone moiety, i.e., 2, 3, 30, 33, 37, and 39, exhibited significant inhibitory activity toward the killing function of CTL and the induction of ICAM-1.